Ethyl vinyl ether → 2-Ethoxy-4-phenyl-3,4-dihydro-2h-pyran

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[CH:9]=[O:10])=[CH:3][CH:2]=1.[CH:11]([O:13][CH2:14][CH3:15])=[CH2:12]>>[CH2:11]([O:13][CH:14]1[CH2:15][CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:8]=[CH:9][O:10]1)[CH3:12]

Participants

Reactant 2

HCID 8023Ethyl vinyl ether

HCID 637511Cinnamaldehyde

Product 1

HCID 2801772-Ethoxy-4-phenyl-3,4-dihydro-2h-pyran

Procedure

treating cinnamic aldehyde with ethyl vinyl ether to afford 2-ethoxy-4-phenyl-3,4-dihydro-2H-pyran, hydrogenating the resulting product to afford 3-cyclohexylpentane-1,5-diol and finally heating the above diol in the presence of a dehydrogenation catalyst to afford 3-cyclohexyl-pentanolide; or

Sources & evidence

ORD record: ord-948df3d4cf5b47b6af07726b82caa3fb
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04251398

Reaction notes

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